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$4,050,000
6 Beds ⋅ 4 Baths ⋅ 24131596 MLS
SUPERB LAKE PROPERTY. First time on the market, this 4,811 sf shingle-style home on 6.99 acres in Lake Quassapaug's estate area offers 195 feet of direct waterfront with a private dock and small beach. Designed by renowned architect Rick Moisan and built in 2000, the residence blends timeless design with modern comfort, enjoying complete privacy and pastoral views of permanently protected neighboring hayfields and vineyards. This rare offering combines architectural pedigree, serene natural beauty, and versatile living spaces-a true sanctuary for lakefront living. TWO PARCELS. Includes the main residence and a charming two-bedroom cottage sold together. MAIN RESIDENCE. Classic shingle-style architecture with a bright, open layout for today's lifestyle. The living room, dining area, and kitchen flow together beautifully; the kitchen features high-end appliances and opens to an inviting sunroom capturing passive solar warmth. Every room enjoys a full or partial landscape view. A deep covered porch spans the lake side for gracious entertaining, sunsets, and al fresco dining. Large Doric columns frame the space, and a majestic oak anchors the open lawn. COTTAGE. Originally the caretaker's residence for historic Tranquillity Farm, this two-bedroom, 1,005 sf cottage on a separate parcel offers wonderful flexibility as a guesthouse, writer's retreat, or rental.

7-11 Sandy Beach Rd, Middlebury
$1,750,000
5 Beds ⋅ 7 Baths ⋅ 170507932 MLS
Exquisite Country Cape situated along one of Middlebury's most picturesque roads. This 5800 sq.ft. Cape is a true gem, boasting a gunite pool, acres of open meadow bounded by stone walls, distant city views & beautiful backyard w/ patio, perfect for hosting summer soirees. Recently renovated, this sprawling home offers a fabulous eat-in kitchen w/ spacious island and a generous dining area featuring a vaulted ceiling w/ exposed hand-hewn beams & FP. A cased opening leads to a sun porch with 3 walls of glass offering seamless access to a private patio.The main level is a showcase of elegance & functionality featuring a formal LR w/ FP & built-ins, a gracious DR w/ corner built-ins, a paneled 1st floor office complete w/ FP & wet bar & a sumptuous primary BR suite. Almost every room treats you to breathtaking distant views of the patio & inviting in-ground pool. The upper level offers a quaint loft area & 3 beautifully appointed BR’s, two of which have en suite baths, resulting in a total of 3 full baths on this floor. The pristine exterior boasts the hallmark Middlebury stone walls adorning the front, fencing, terraced patios, in-ground pool, practice golf range for enthusiasts & acres of lush meadow for your enjoyment. Additional amenities include a 2nd first-floor BR suite, an attached 3 car garage & a drive-under garage that provides multi-car storage space in the basement. Situated in the highly sought-after South Street location, this property is an exceptional find.

700 South St, Middlebury
$1,750,000
4 Beds ⋅ 7 Baths ⋅ 24020405 MLS
Stunning all brick home w/ heated in-ground pool, covered outdoor dining/entertaining space and main level master set on a private lot on a cul-de-sac of similar homes. In-ground pool w/ spa, fully applianced and covered outdoor kitchen w/ entertaining area, bar, fireplace and ample room for sitting. Poolhouse. Putting greens. Gorgeous patio w/ pergula. Inside, remodeled eat-in-kitchen w/ granite countertops, large center island, Stainless Steel appliances including 6 burner Wolf stove, Subzero fridge, wine fridge, potfiller, pantry and 2 sinks. Family room w/ fireplace open to kitchen area. 2-story formal living room w/ applianced wetbar and fireplace. Grand dining room. Study w/ rich wood paneling and ceiling. Main level master suite w/ fireplace, trey ceiling, walk-in closet w/ built-ins, and attached full bath w/ marble floor, tile surround shower, double sink and jetted tub. Main level laundry room w/ granite. 2 main level powder rooms. 3 additional bedrooms upstairs all with an attached bath and ample closet space. Bonus room upstairs. Tastefully finished lower level with gorgeous trimwork and fireplace, wine room, home gym, and potential for even more finished space. High ceilings and beautiful trimwork throughout. Mechanicals include central air, propane heat, audio, generator, sec system, central vac. New roof and many very recent updates. The facade, curb appeal and entertaining area are absolutely striking. Don't miss the chance to have your own private estate!

40 Winthrop Dr, Middlebury
$1,700,000
3 Beds ⋅ 3 Baths ⋅ 170589536 MLS
This custom arts and crafts bungalow, designed and built for its current owners, is perfectly sited on 14.85 tranquil acres, highlighting a gorgeous view and is accessed by a long gated private driveway. It is a home for someone who loves nature, stone and wood in a very private setting. The timeless design and easy layout are embellished by fine craftsmanship and quality materials which include quarter-sawn white oak floors, doors and trim with 9’ ceilings. The foyer entryway leads to a study, pantry and mudroom with half bath. The living room fireplace was crafted with stone carefully selected from the property. The sun filled kitchen with casual dining includes Crown Point cabinetry, Wolf, Subzero and Bosch appliances with access to the terrace, gardens and conservatory. The main floor primary suite has his/her closets, laundry room, full bath and terrace access. Upstairs is the family room, office nook, two bedrooms and full bath. A walk-out lower level has recreation space, wine room, sauna and gym as well as Veissmann mechanicals, with hydronic 5-zoned radiant heated floors throughout, audio system, Unico central A/C system and 12kw Kohler generator. Multiple outbuildings include two (2 bay) heated garages with epoxy floors, equipment barn (can fit 2 cars) with greenhouse, potting and wood sheds, outdoor fireplace and shower, electric awnings and an in-ground rainwater cistern for garden irrigation. Turnkey mint.

397 White Deer Rock Rd, Middlebury
$1,375,000
4 Beds ⋅ 5 Baths ⋅ 24096103 MLS
Welcome to this expansive and exquisitely renovated Colonial estate, where timeless charm meets modern luxury. Boasting 5 spacious bedrooms and 5 elegantly appointed bathrooms, enhanced by a fully finished lower level offering potential for an in-law apartment or guest suite. Designed with flexibility and functionality in mind, the home features multiple flex rooms that can easily serve as dedicated home offices, creative studios, or fitness spaces-perfect for today's dynamic lifestyles. The large open floor plan seamlessly connects the gourmet kitchen, formal dining, and airy living areas, creating an ideal environment for entertaining or simply enjoying everyday living with ease and elegance. Step outside to your private backyard oasis-featuring a tranquil koi pond, an oversized outdoor pool, a dedicated lap pool for fitness enthusiasts, and a relaxing hot tub tucked beneath mature trees. Whether you're hosting guests or seeking a quiet escape, this outdoor retreat delivers a true sense of serenity and luxury. This one-of-a-kind property offers space, versatility, and high-end comfort-perfect for those who value refined living in a serene, resort-like setting.

122 Mirey Dam Rd, Middlebury
$1,360,000
5 Beds ⋅ 5 Baths ⋅ 170613102 MLS
This 1929 stately 5800 sqft custom colonial, sitting on nearly 4 acres in the heart of Middlebury, has been completely updated and restored, both inside an out. Expertly combining classic elegance and modern updates making this a truly spectacular opportunity to purchase your dream home! This spacious, vintage home boasts three levels of living space, with new Marvin and Anderson windows throughout. Custom kitchen is a chef's dream with wolf double ovens, sub-zero refrigerator and freezer, oversized Carrara marble island, plenty of storage, built-in hutch and spacious eat in area. Large dining room with built ins, plus living room and family rooms with coffered ceiling, each with their own fireplace. Hardwood floors complete the main living space. Relax in the elegant primary suite, with fireplace, spacious walk in closet, luxurious bath with Carrara marble, soaking tub plus Juliet balcony overlooking the beautiful grounds. Two additional bedrooms and den on the second floor make it a perfect space for lounging or studying. The third floor offers two rooms and newly remodeled bath. The 4 season sunroom welcomes you outdoors to enjoy lush landscaping, covered patio perfect for entertaining with built in bbq and fire pit with ample seating. An in ground pool with spa and patio surround completes this entertainer's dream. An impressive circular driveway with stonewalls will greet your guests. A fabulous, private retreat just 90 miles from NYC and minutes from Oxford airport.

Middlebury
$1,300,000
4 Beds ⋅ 7 Baths ⋅ 170594586 MLS
Come enjoy a unique, elegant, old-world experience designed with artful accents and architectural accentuations throughout. The grand sweeping foyer with porcelain & marble tile flooring, the curved custom stairway, and the 20’ ceiling mirrors that of the grande European Manors. The authentic reproduction of the French porcelain flooring, coupled with multiple French & English influences elevates this estate home to a level of art and elegance. The splendid formal living room boasts a circa 1776 antique French chestnut mantel accenting a hand-built limestone fireplace. The 12’ ceilings with hand-sculptured beams magnify the exhilarating sense of space felt throughout this stunning manor. The striking conservatory encompassed by a dynamic amount of glass illuminates the blue stone floors and brick trim. A focus point of the elegant dining room is the double-tier octagonal tray ceiling along with the custom hand-painted stencils continued from the living room through to the kitchen. The flow of the living space extends out onto the blue stone terrace with private views of the magnificent and fragrant perennial gardens framed with brick and stone. The captivating French country kitchen equipped with custom cabinets, high-end appliances, center island breakfast bar continues to provide a great space for entertaining and relaxing. Completing the first floor are the walnut-paneled Library, office, a huge cedar-clad porch, and the expansive Master Suite. Continued in public remarks.

7 E Farm Rd, Middlebury
$1,250,000
3 Beds ⋅ 4 Baths ⋅ 170608436 MLS
Nestled amidst the rolling hills this architectural gem exudes timeless charm and offers a luxurious lifestyle within a serene setting. The heart of the home is the chef's kitchen, complete with premium appliances, custom lighting, and cork flooring. An inviting living room boasts a magnificent stone fireplace and radiant heat, providing the ideal space for relaxation. The primary suite is an oasis of luxury, featuring a spacious layout, a cozy fireplace, an elegant walk-in closet and a spa inspired en-suite. Adjacent to the suite, the yoga studio offers a serene space to find balance and focus. The office, with vaulted ceilings and french sliders to the back, is perfect for remote work. Spectacular views unfold through expansive Marvin windows, offering a picturesque backdrop to your daily life. The lower level presents additional bedrooms, a game room, and a kitchenette, perfect for entertaining. Smart features such as Lutron lighting, wired sound, and an on-demand generator add convenience and peace of mind. Outdoors, a bluestone patio encircled by indigenous rock walls and a small waterfall creates a tranquil oasis. The meticulously landscaped grounds offer year-round beauty, while mature trees and evergreens ensure privacy. Situated just two hours from the vibrant energy of NYC, this property provides the perfect balance of luxury and accessibility. With heated floors, UV films on windows, and countless other amenities, it redefines the essence of gracious living.

92 Chesham Dr, Middlebury
$1,219,659
3 Beds ⋅ 3 Baths ⋅ 24022962 MLS
New construction will impress the most discerning buyer. The Cambridge Model with 2,878 sq. ft. offers a grand two-story foyer leading to the great room with soaring ceilings, fireplace and beautiful windows giving the space a light and airy feeling. The kitchen and heart of the home has an expansive island, granite countertops, stainless steel appliances and white shaker style cabinets. For informal dining a breakfast nook off the kitchen has French doors leading to the back deck. A formal dining room for those special occasions rounds out the flow for ease of entertaining. The first-floor primary suite offers two walk-in closets and a luxurious bath with oversized shower and double vanities. The second level, with two generously sized bedrooms, share a Jack and Jill bathroom. A den tucked away on the first floor offers options for working from home, relaxing with a good book or home schooling. All hardwood floors run throughout the main level. There is a first-floor laundry, mudroom, 2 car attached garage, c/a, underground utilities, underground sprinklers, public water and sewer and natural gas. This lot enjoys the pricvacy of a cul de sac location. Photos used are similar to new construction; pictured lighting is not included. Floor plans, elevations are attached.

25 Somerset Dr, Middlebury
$1,100,000
3 Beds ⋅ 4 Baths ⋅ 170581926 MLS
Welcome to Luxury. This completely renovated custom-built home is privately nestled on a quiet cul-de-sac on over 2 acres of professionally landscaped gardens, lawns, and beautiful stone walls. Boasting Custom Marvin windows and doors, wide white oak hardwood floors, along with custom trim are what makes this home exceptional. Beautiful natural light fills all the rooms. Through the marble foyer you enter the library-office area or can step down into the stunning living room with cathedral ceilings, custom limestone fireplace and floor to ceiling windows with beautiful views of the outdoors. The living room opens to a spacious formal dining room with French doors that lead to the beautiful back yard with plenty of space for large family gatherings. You will appreciate the seamless flow of the entire first floor, which is ideal for entertaining. The chef’s kitchen features furniture-quality custom made cabinetry with all Wolf stainless steel appliances including a 6-burner cook top with indoor grill, pot filler, 3 ovens, subzero, wine cooler, warming drawer, 2 dishwashers, large pantry, 3 sinks, extra-large center Island and coffee/bar area. The eat in breakfast area has cathedral ceilings, a chandelier, and French doors leading to back yard. Continue into the large family room as well as the laundry room/hobby room/office both including custom cabinets. Off these rooms are 4 smart climate-controlled garages perfect for the car enthusiast. ...

17 Beacon Hill Rd, Middlebury
$1,100,000
4 Beds ⋅ 6 Baths ⋅ 24080272 MLS
Over 5000 total finished sqft in this gorgeous custom colonial with 3 car garage situated on 1.84 acres in a neighborhood of like homes. Grand entry foyer and 9ft ceilings throughout the main level. Eat-in-kitchen with hard wood floors, island, breakfast bar, pantry, granite countertops, and high end stainless steel appliances including double oven, propane cooktop, and Sub Zero refrigerator. Kitchen is open to sun drenched family room with fireplace and hardwoods. Dining room with simulated paneling, crown molding, hardwood floors with cherry overlay, and french doors. Formal living room could be used as a study/office with more paneling, french doors, and crown. Magnificent master suite with hardwood floors, trey ceilings, balcony deck, 2 walk-in closets, and attached full bath, sitting room, and office. Master bath has dual vanities with marble countertops, jetted tub, and stand up shower. Sitting room with propane fireplace and built-ins. Office with french doors and crown molding. Secondary bedroom suite with walk-in closet, attached full bath, and additional sitting room. 3rd and 4th bedrooms both with additional bathrooms attached. Quality millwork throughout. California closets. Finished basement with rec room, bar area, and additional half bath. Plenty of room for storage. Gorgeous backyard setting with paver patio and firepit set on a pristine lot with stone walls and privacy. Strong mechanicals including irrigation, generator, security, hydro and central air.

45 E Farm Rd, Middlebury
$1,050,000
5 Beds ⋅ 7 Baths ⋅ 170527394 MLS
Stunning Colonial design with three floors of idyllic living space. Gorgeous five bedroom, six full & a half bathroom, custom built with classic features. Beautiful architectural details throughout, including a huge foyer, uniquely designed floor plan on each level, spacious rooms, built-ins, huge ground & upper-level patio, hardwood flooring & more. All surrounded by five acres & privacy. Come and bring your ideas to add, creating the perfect home for you and your lifestyle. Although part of a quiet subdivision, this house was designed and built by a separate architect and contractor for the sellers. The great room boasts two walls of windows and is open to the informal dining area. The sizeable kitchen, boasting distinctive cabinets, a fabulous center island and an abundance of counterspace. Features that please even the most persnickety chefs! Microwave not operational. The Master Suite is off a long hallway. A span of built-ins along one wall creates a chic expansive space. True architectural attention to every detail. Upstairs there are three bedroom suites off a large central space. One, a potential second master & the other two with a wall of windows opening to a huge terrace. The lower level boasts an au pair suite with second kitchen. You will be amazed with the space and storage in this home. Conveniently located near I 84 for commuting access. Area amenities nearby, local private schools include The Taft School and Westover School.

54 Falcon Crest Rd, Middlebury
$1,000,000
4 Beds ⋅ 4 Baths ⋅ 170597325 MLS
New Constructions

106 Judd Hill Rd, Middlebury
$975,000
4 Beds ⋅ 3 Baths ⋅ 24131272 MLS
Welcome to 82 Mirey Dam Road, Middlebury, CT, a stunning colonial oasis tucked away on 2.74 acres of mature, peaceful landscaping in one of the area's most sought-after neighborhoods. From the moment you arrive, you'll feel the sense of calm this property conveys. Lush landscaping, mature trees, and careful design grant privacy and serenity. The heated saltwater inground pool and outdoor spaces invite you to relax, entertain, and savor every season in your own personal retreat. Inside, the flow is effortless. The freshly painted interior, upgraded windows, and modern lighting set an elevated tone. The fully renovated bathrooms blend style and practicality. Bedrooms are generous with stunning views and light-filled; common rooms are versatile and ideal for both daily living and special occasions. Every major system and feature of this home has been thoughtfully updated, creating a move in ready property with style and reliability. A detailed list of all upgrades is attached to the listing highlighting the extensive improvements that make this property truly move-in ready.

82 Mirey Dam Rd, Middlebury
$950,000
4 Beds ⋅ 4 Baths ⋅ 24087126 MLS
This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors, loft area & an attached green house! The main house features a grand foyer with granite flooring, a very large, formal dining room & a generous sized formal living room/music room. The eat-in kitchen area is large enough to hold an 8 seat table & chairs & has slider access to the deck. There is an island in the center of the kitchen with additional seating as well stainless steel appliances & a work area. As you walk down the hall to the 3 car garage you will pass another smaller study with builtins & an exceptionally large pantry & mudroom area. There is a separate laundry room & 1/2 bath. The sizable great room has a fireplace, bar area & sliders to the enormous deck! On the deck is where you can relax or entertain by the outdoor fireplace & cook in the custom pizza oven! There is also an oversized main floor office for those who work from home or need a guest area. This office has a fireplace, built-ins & another full bath. Upstairs is the Primary Suite with a walk in closet, full bath featuring a jacuzzi tub, separate shower & 2 sinks. The main bathroom also has double sinks & a tub with shower. There are 3 other large sized bedrooms with hardwood flooring & plenty of closet space. The enormous basement has a rolling garage type door if you need to store anything with easy access! The possibilities are endless!

593 Park Road Ext, Middlebury
$950,000
4 Beds ⋅ 4 Baths ⋅ 24016070 MLS
This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors, loft area & an attached green house! The main house features a grand foyer with granite flooring, a very large, formal dining room & a generous sized formal living room/music room. The eat-in kitchen area is large enough to hold an 8 seat table & chairs & has slider access to the deck. There is an island in the center of the kitchen with additional seating as well stainless steel appliances & a work area. As you walk down the hall to the 3 car garage you will pass another smaller study with builtins & an exceptionally large pantry & mudroom area. There is a separate laundry room & 1/2 bath. The sizable great room has a fireplace, bar area & sliders to the enormous deck! On the deck is where you can relax or entertain by the outdoor fireplace & cook in the custom pizza oven! There is also an oversized main floor office for those who work from home or need a guest area. This office has a fireplace, built-ins & another full bath. Upstairs is the Primary Suite with a walk in closet, full bath featuring a jacuzzi tub, separate shower & 2 sinks. The main bathroom also has double sinks & a tub with shower. There are 3 other large sized bedrooms with hardwood flooring & plenty of closet space. The enormous basement has a rolling garage type door if you need to store anything with easy access! The possibilities are endless!

593 Park Road Ext, Middlebury
$937,500
5 Beds ⋅ 3 Baths ⋅ 24167191 MLS
Welcome to this beautifully updated home which offers modern comfort, high-end finishes & peace of mind with several upgrades already completed! Located in Middlebury's South Street neighborhood this Colonial is 3300 sq ft on a 1.85 acre lot. Step in to a bright & inviting foyer feat. a high ceiling, a custom wood & glass front door & a stunning custom handrail leading the expansive 4 bedrooms. On the main level you will find a formal living room with coffered ceilings, French doors & a large dining room with plenty of room for gathering to enjoy a meal.The spacious great room offers a gas fire place, gleaming HW floors & French doors leading out to an oversized deck as well as a custom stone patio w/a built-in fire pit surrounded by a stone wall & beautiful gardens. The chef's kitchen is the heart of the home where everyone gathers around d the kitchen island. Seating around the breakfast bar with quartzite counters is the perfect spot to enjoy a cup of coffee in the morning. Included in the dream kitchen is a 6 Burner Thermador, range/oven, a SS Subzero side by side refrigerator, a SS microwave tucked neatly in the island, a SS dishwasher & a large farm sink. An oversized powder room & nice sized office finish off the first floor. Upstairs the Primary Suite features a tray ceiling, walk-in California Closet w/plenty of storage & new tile flooring. The on Suite to the Primary has heated Calcutta Gold Marble flooring, custom vanity, walk-in, extra large shower & soaking tub.

851 South St, Middlebury
$930,000
4 Beds ⋅ 4 Baths ⋅ 170620693 MLS
A seamless blend of sophistication and tranquility in this exquisite home. The curb appeal is nothing short of spectacular, featuring a classic brick exterior, professionally landscaped surroundings, and a dramatic front entrance. Upon entering the two-story foyer, the meticulous details of the formal dining and living rooms unfold with archways, custom curtains, coved ceilings, and adorned walls. Ascend the open stairway to the top floor, where a balcony overlooks the main living space, creating an inviting atmosphere. Enter the sunken family room, where large windows, cathedral ceilings, and a stone gas fireplace welcome you. This space seamlessly connects to the custom kitchen, boasting abundant cabinet space, two Wolfe Ovens, a custom-built hood vent, Subzero refrigerator, and a wine cooler. The sunroom provides a picturesque view of the heated pool, hot tub, expansive green yard, and the surrounding Clark Land Trust, transforming the property into a private oasis. Retreat to the main level master en suite at the end of the day, where luxury continues with a gas log fireplace, his and hers walk-in closets, and a spa like bathroom for ultimate pampering. The upper level accommodates two bedrooms with walk-in closets and a Jack and Jill bathroom, along with a third bedroom and full bath. The home is equipped with modern amenities, including a new whole house generator, a Buderus Furnace, an on-demand tankless hot water heater, and a new water softener system.

429 Mirey Dam Rd, Middlebury
$900,000
4 Beds ⋅ 3 Baths ⋅ 24179200 MLS
Set in one of Middlebury's most desirable neighborhoods, this lovingly maintained 4,450 sq. ft. Colonial welcomes you with a beautiful paver driveway, manicured lawn, and timeless curb appeal. Step inside the sunny two-story foyer and feel right at home. The spacious eat-in kitchen is designed for gathering, featuring granite counters, a center island, breakfast bar, and generous dining area. For more intimate occasions, enjoy the formal dining room and living room with fireplace. The grand first-floor cathedral family room offers a second cozy fireplace and atrium doors leading to an expansive paver patio with firepit, perfect for outdoor entertaining The main level also includes a welcoming sunroom, office or optional bedroom, full bath, and spacious laundry room with abundant storage. Upstairs, you'll find four generously sized bedrooms and a full hall bath, including a primary suite with private bath, jetted tub, shower, double sinks, and a walk-through closet. A 25' x 16' great room with separate access to the 3-car garage offers excellent flexibility for a home office, gym, recreation space, or potential in-law setup. A wonderful opportunity to enjoy space, comfort, and versatility in a sought-after Middlebury setting.

286 Mirey Dam Rd, Middlebury
$895,000
4 Beds ⋅ 5 Baths ⋅ 24141215 MLS
Welcome to your dream home...a beautifully designed 3220 sq ft NEW CONSTRUCTION offering warmth, space and flexibility for today's modern family. With 4 generous bedrooms and 4.5 bathrooms, this home invites you to live, laugh and grow in comfort. You have to see in person to appreciate the design of each of the bedrooms with their one full bath and double closet space. The heart of the home is the open concept main level, where the kitchen, dining and living areas come together around a cozy electric fireplace- perfect for family dinners, holiday gatherings, or quiet evenings in. The chef's kitchen is as functional as it is stunning, featuring granite countertops, tiled backsplash, double ovens, a large island ideal for casual meals and an abundance of cabinets for all your kitchen treasures. Step through the sliding doors to a spacious trex deck(16x12), perfect for morning coffee or weekend barbecues. Stairs led you down to a charming patio and walkway the wraps around the home- an entertainer's dream and safe place to play and explore. The lower level is designed with versatility in mind- a warm family room, a private bedroom with half bath (easy convertible to full) for guests or possible in law setup and another full bathroom with a second laundry hook-up for more convenience. Upstairs, the peaceful oversized primary suite is your personal retreat complete with a large walk-in closet and a spa-like bathroom featuring a soaking tub, glass shower and double vanities

383 Leonard Rd, Middlebury
$895,000
4 Beds ⋅ 4 Baths ⋅ 24023563 MLS
Welcome to your dream home! This one-owner custom-built residence is nestled in the heart of one of Middlebury's most sought-after neighborhoods. Offering the perfect blend of luxury, comfort, and convenience, this stunning property features a large and luxurious light filled primary bedroom and bathroom suite. There are 3 additional bedrooms on the second floor and 2 full baths. The first floor has an inviting foyer, office, formal living room with a fireplace and dining room both with parquet flooring. The kitchen is very large and open to the family room, dining area and sitting room. The basement is finished for additional recreation and/or home gym space. There is a Generac propane generator for added comfort and convenience. This one of a kind home offers a seamless blend of indoor and outdoor living spaces, designed to provide an exceptional lifestyle. The large patio is perfect for summer barbecues and evening gatherings, while the heated pool and tennis court make this home a place you will never want to leave!

122 Northridge Dr, Middlebury
$882,500
5 Beds ⋅ 4 Baths ⋅ 24104524 MLS
Welcome to 171 Judd Hill Road, a stunning custom built home with high end finishes throughout, nestled in the quiet beauty of Middlebury CT. Built in 2015, this immaculately maintained 5 bed, 4 bath home offers thoughtful design, with a separate in-law suite plus additional 400 SF of unfinished basement for extra storage. The main level features hardwood floors, a sun-filled two-story foyer and great room with fireplace, formal dining room and open-concept eat-in kitchen. The main level primary suite includes a walk-in closet, full bath, and a separate office - perfect for remote work (or can be used as a 2nd closet). A 2nd bedroom with full bath also on main floor. Upstairs are 2 bedrooms, 1 full bath, plus versatile bonus room ideal as a media space or 6th bedroom. Downstairs, a fully soundproofed 1 bed apartment with ensuite bathroom, full kitchen, laundry, fireplace, and home gym offers endless options for multigenerational living, guest space, or an income-producing rental. Enjoy long views from the back deck and bonus features like a well-organized laundry/mudroom and second fridge & freezer in the garage. Set in a quiet neighborhood with access to top-rated public & private schools, Lake Quassapaug, parks, trails, and just minutes to I-84 and Middlebury's town center. A rare find in one of New Haven County's most welcoming communities.

171 Judd Hill Rd, Middlebury
$875,000
3 Beds ⋅ 3 Baths ⋅ 24167463 MLS
Enjoy magnificent sunsets from this exceptional home, privately set on just over three acres in one of the area's most desirable locations. The beautifully landscaped grounds offer both open space and a wooded backdrop for added privacy, along with views of a neighboring stone wall. An in-ground heated saltwater pool is surrounded by an expansive patio and charming pergola-perfect for outdoor entertaining. Three garages are conveniently accessible from both the upper and lower driveways. Inside, the home features 2,990 square feet of thoughtfully designed living space with custom touches throughout. The spacious kitchen includes a dining area, breakfast bar, and a 36" GE Monogram dual-fuel range, offering ample space for cooking and gathering. The adjoining 23' x 20' family room provides a welcoming setting, a propane fired custom fireplace and overlooks the scenic rear property. The primary suite features a walk-in closet, an additional closet, and an updated full bath. The main level is completed by a formal dining room, private office/library, powder room, and laundry area. Upstairs, you'll find two additional bedrooms, a full bath, and a flexible guest area and lots of room for expansion. Additional highlights include the lush grounds, patio, heated saltwater pool, pergola, and more.

245 Upper Whittemore, Middlebury
$852,250
6 Beds ⋅ 4 Baths ⋅ 170619078 MLS
HIGHEST & BEST BY MONDAY, 1/29 AT NOON. Discover timeless elegance in this historic home built in 1815, nestled in a prime location w/a 4.3-acre approved building lot. Experience the charm of yesteryear w/a captivating wrap-around porch adorned w/stone pillars, inviting you to indulge in the surrounding scenery. Boasting 14 rms, including 6 bdrms & 3 and 1/2 baths, this residence exudes a classic charm enhanced by wood floors thru-out. Step into a grand entry w/a majestic staircase, setting the tone for the home's historic significance. The spacious living room features a welcoming fireplace, creating a cozy ambiance perfect for gatherings.The kitchen, complete with breakfast nook & its own fireplace, adds a touch of warmth & functionality. Imagine enjoying your morning coffee bathed in the natural light pouring through large windows that grace every room, offering a picturesque view of the expansive 5.65-acre property. Curb appeal is at its finest, w/a recently refreshed exterior that enhances the home's timeless allure. Immerse yourself in the character of this gem, where history meets modern comfort. Seize the opportunity to own a piece of the past while embracing the possibilities of the future on the approved building lot. Don't miss the chance to make this historic residence your forever home. Embrace a lifestyle that seamlessly blends the elegance of the past with the conveniences of the present. Your dream home await.

249 South St, Middlebury
$850,000
3 Beds ⋅ 3 Baths ⋅ 24168079 MLS
Welcome to your own private retreat at 122 Crest Road-where timeless charm meets thoughtful modern updates. This beautifully maintained 3-bedroom, 2.5-bath Cape Cod-style home is just moments from town, the library, green, and local dining. Designed with both everyday living and entertaining in mind, the home features a custom sunken great room with a dramatic wall of windows that floods the space with natural light and showcases the surrounding landscape. Sliding doors lead seamlessly to a bluestone patio, creating indoor-outdoor flow. The kitchen has new appliances and opens nicely to the great room, enhancing the home's open feel. For more formal gatherings, enjoy the elegant dining room with French doors leading to a charming screened porch, as well as a separate formal living room featuring a fireplace and custom built-ins. Wide plank hardwood flooring adds warmth and character throughout much of the home. A dedicated study offers a cozy fireplace and built-ins-perfect for a home office or quiet retreat. The main-level primary suite is a very nice convenience. Extensive recent upgrades include a new roof, new Hardie board siding, new gutters, new central air system (including air handler), new boiler, new windows, and a security system. Professionally landscaped grounds, mature trees, stone walls and bluestone create a serene setting, yet remains close to everything. Includes a whole house generator. A full list of improvements is available. 90 miles to NYC.

122 Crest Rd, Middlebury
$830,000
4 Beds ⋅ 3 Baths ⋅ 24062216 MLS
Attention to detail is evident throughout this custom 4-bedroom beauty. The home placement was intentional, allowing you to wake up to a sun-filled kitchen and end the day with a sunset from the sprawling teak wood front porch that overlooks an organic lavender farm. The kitchen is designed for the house's chef, featuring high-end appliances such as Capital double ovens, a warming drawer, and a 6-burner gas cooktop, as featured on the Food Network. The open floor plan is perfect for entertaining or cozying up by the fireplace in the great room. The home was designed with two front door entrances: one for guests and the other with the potential for an at-home office entrance, complete with a second staircase to the bonus room or playroom, which includes a spacious laundry room with cabinets and plenty of room for folding. Additional details include a Sonos surround sound system, high-end lighting fixtures, and European hand-blown glass kitchen pendants above the kitchen island. The full basement with a walkout is rough-plumbed for a bath and ready for future finishing. Outdoor features include high-end vinyl shakes, a slate patio, and a garden area. Enjoy all that Middlebury has to offer, including walking trails, nearby Lake Quassapaug, shopping, and fine restaurants. This home combines luxury, comfort, and convenience in a beautiful setting.

340 Burr Hall Rd, Middlebury
$820,000
4 Beds ⋅ 3 Baths ⋅ 24055021 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 11 Hunting Ridge Road (aka Lot 3) is to be built. It is a 2700 sq ft colonial with 2 car attached garage.Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office. The primary bedroom boasts walk-in closet with custom shelving and private full bath. There are several other lots and plans to choose from or will build to suit! City water and sewer !!

11 Hunting Ridge Rd, Middlebury
$818,266
2 Beds ⋅ 3 Baths ⋅ 170547594 MLS ⋅ Granite Woods BLDG.
Welcome to Granite Woods, a unique, brand new in-town 55+ home community featuring 24 Cape-style classic homes in the heart of tranquil Middlebury Village, walkable to restaurants, coffee shops, shopping, and direct access to the popular Middlebury Greenway Trail. Phase One is currently underway offering five unique designs that make living in style easy for years of family enjoyment while emphasizing the ease of aging in place, with no step front entries and wide interior door openings. Amenities include a for-residents-only pickleball court, shuffleboard, and pavilion. The Ash with a New England-style portico welcomes you to this home. As you enter through the foyer there is an adjacent flex room with a nearby powder room. The large, bright great room features a gas fireplace and is the perfect space for family gatherings. A first-floor owner’s suite complete with a walk-in closet offers views of the quiet backyard. A handy mudroom offers a bench seat and extra storage, while an adjacent laundry room completes the first floor. The second floor offers a second bedroom with a bathroom and a large loft. The beauty, craftsmanship, customization, and attention to detail these homes offer, along with Award Winning Builders' project expertise, will ensure an enjoyable experience and future at Granite Woods. Nothing is as rewarding as customizing your home, let’s work together to make your dream home a reality! Alternate Plans Available!! Property owners have a Real Estate License

6 Oakwood Dr Unit 11, Middlebury
$815,000
3 Beds ⋅ 3 Baths ⋅ 24180471 MLS
Welcome to Avalon Farms community, located in one of Middlebury's distinctive residential communities, known for its beautifully built, upscale homes. The home is known for its European inspired architecture, beautifully preserved, natural surroundings, at the end of a cul-de-sac, which suits any stage of life you're in. Step inside to a grand two-story foyer that sets the tone for the homes spacious, filled with natural light. This 3 bedroom, 2.5 bath home has an open floor plan great for entertaining. The primary bedroom situated on the first floor, features a coffered ceiling, a generous walk-in closet, with a spacious bathroom complete with a walk-in shower & whirlpool tub. Directly off the primary bedroom there are endless opportunities, whether that space may serve as a nursey, office space or play area. The kitchen serves as the heart of the home, featuring a spacious granite island, abundant cabinetry, and plenty of storage perfect for everyday living, entertaining, and gathering with family & friends. Conveniently off the kitchen you have first floor laundry in its own dedicated space with a utility sink and tons of storage space. Two spacious bedrooms & a full bathroom complete the upstairs and if you needed more space you will find a heated finished basement as well.

38 Avalon Dr, Middlebury
$815,000
4 Beds ⋅ 4 Baths ⋅ 170603544 MLS
This 4 bedroom Colonial is situated on 3.63 acres surrounded by stone walls, mature trees, land trust property, walking trails and an abundance of privacy. The view from your windows will only change with the seasons! The generous, open floor plan of this impeccable home is awash in natural light creating comfortable and inviting spaces to relax and entertain both inside and out. The foyer is flanked by formal living and dining rooms, each with hardwood floors. The 2 story family room is the stunning showpiece of this home. It features a wall of windows and sliders with views of the natural landscape and a floor to ceiling stone fireplace. The family room is open to the well appointed kitchen with solid wood cabinetry, tile flooring and a large Thermador gas range for the most discerning chef. The first floor continues with an office, large laundry room, mud room/side entryway and a full bath. The second level of the home offers nice separation via catwalk between the primary wing and 3 additional bedrooms and full bath. The primary suite offers large walk in closets, a dressing/sitting area and bathroom with double sinks, tiled shower and jacuzzi tub. All of this - plus a large finished basement with a recreation room, workout area and a half bath. The detached 3 car garage offers additional space above that may be finished in the future. You will not want to miss the opportunity to view this one-owner custom home. 5 minutes to I84 & Rt. 8, 90 minutes to New York City.

191 Falcon Crest Rd, Middlebury

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